PL94249B1 - - Google Patents
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- Publication number
- PL94249B1 PL94249B1 PL1975180819A PL18081975A PL94249B1 PL 94249 B1 PL94249 B1 PL 94249B1 PL 1975180819 A PL1975180819 A PL 1975180819A PL 18081975 A PL18081975 A PL 18081975A PL 94249 B1 PL94249 B1 PL 94249B1
- Authority
- PL
- Poland
- Prior art keywords
- hydrochloride
- general formula
- isopropanol
- pattern
- salt
- Prior art date
Links
- -1 unsaturated cycloalkyl radical Chemical class 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 229940123208 Biguanide Drugs 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000004283 biguanides Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 6
- 150000001412 amines Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 4
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical group [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 28
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 238000009835 boiling Methods 0.000 description 8
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000012280 lithium aluminium hydride Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 description 2
- UBLYEVLMRSPMOG-UHFFFAOYSA-N cyclopentylmethanamine Chemical compound NCC1CCCC1 UBLYEVLMRSPMOG-UHFFFAOYSA-N 0.000 description 2
- 229910001385 heavy metal Inorganic materials 0.000 description 2
- 229910003439 heavy metal oxide Inorganic materials 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- GUESPPPRHQUWDW-UHFFFAOYSA-N 2-(cyclobutylmethyl)-1-(diaminomethylidene)guanidine;hydrochloride Chemical compound Cl.NC(=N)NC(=N)NCC1CCC1 GUESPPPRHQUWDW-UHFFFAOYSA-N 0.000 description 1
- KGSORAUUADWSEQ-UHFFFAOYSA-N 2-(cycloheptylmethyl)-1-(diaminomethylidene)guanidine;hydrochloride Chemical compound Cl.NC(=N)NC(=N)NCC1CCCCCC1 KGSORAUUADWSEQ-UHFFFAOYSA-N 0.000 description 1
- LVHSYCQOYRLSTF-UHFFFAOYSA-N 2-(cyclopentylmethyl)-1-(diaminomethylidene)guanidine;hydrochloride Chemical compound Cl.NC(=N)NC(=N)NCC1CCCC1 LVHSYCQOYRLSTF-UHFFFAOYSA-N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 244000248349 Citrus limon Species 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 208000001647 Renal Insufficiency Diseases 0.000 description 1
- 229920002472 Starch Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 206010046865 Vaccinia virus infection Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical class [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001409 amidines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 229960004111 buformin Drugs 0.000 description 1
- XSEUMFJMFFMCIU-UHFFFAOYSA-N buformin Chemical compound CCCC\N=C(/N)N=C(N)N XSEUMFJMFFMCIU-UHFFFAOYSA-N 0.000 description 1
- FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical class [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 239000001913 cellulose Chemical class 0.000 description 1
- 229920002678 cellulose Chemical class 0.000 description 1
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 1
- LQNHRNOPWKZUSN-UHFFFAOYSA-N cyclobutylmethanamine Chemical compound NCC1CCC1 LQNHRNOPWKZUSN-UHFFFAOYSA-N 0.000 description 1
- CGZZMOTZOONQIA-UHFFFAOYSA-N cycloheptanone Chemical compound O=C1CCCCCC1 CGZZMOTZOONQIA-UHFFFAOYSA-N 0.000 description 1
- 125000000323 cyclohepten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- CAOQEOHEZKVYOJ-UHFFFAOYSA-N cycloheptylmethanamine Chemical compound NCC1CCCCCC1 CAOQEOHEZKVYOJ-UHFFFAOYSA-N 0.000 description 1
- QEYHQERVRCNZHN-UHFFFAOYSA-N cyclohexylmethylazanium;chloride Chemical compound Cl.NCC1CCCCC1 QEYHQERVRCNZHN-UHFFFAOYSA-N 0.000 description 1
- MSXJLEPWWWZERM-UHFFFAOYSA-N cyclopentylmethanamine;hydrochloride Chemical compound Cl.NCC1CCCC1 MSXJLEPWWWZERM-UHFFFAOYSA-N 0.000 description 1
- IGSKHXTUVXSOMB-UHFFFAOYSA-N cyclopropylmethanamine Chemical compound NCC1CC1 IGSKHXTUVXSOMB-UHFFFAOYSA-N 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 206010012601 diabetes mellitus Diseases 0.000 description 1
- 235000019700 dicalcium phosphate Nutrition 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- YKWNUSJLICDQEO-UHFFFAOYSA-N ethoxyethane;propan-2-ol Chemical compound CC(C)O.CCOCC YKWNUSJLICDQEO-UHFFFAOYSA-N 0.000 description 1
- 239000004088 foaming agent Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- AHAREKHAZNPPMI-UHFFFAOYSA-N hexa-1,3-diene Chemical compound CCC=CC=C AHAREKHAZNPPMI-UHFFFAOYSA-N 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 201000006370 kidney failure Diseases 0.000 description 1
- 230000006651 lactation Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910000474 mercury oxide Inorganic materials 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- SDDKIZNHOCEXTF-UHFFFAOYSA-N methyl carbamimidothioate Chemical compound CSC(N)=N SDDKIZNHOCEXTF-UHFFFAOYSA-N 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000008107 starch Chemical class 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000000454 talc Chemical class 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C279/00—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C279/20—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylguanidines
- C07C279/24—Y being a hetero atom
- C07C279/26—X and Y being nitrogen atoms, i.e. biguanides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19742426683 DE2426683A1 (de) | 1974-06-01 | 1974-06-01 | Biguanide und verfahren zu deren herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL94249B1 true PL94249B1 (de) | 1977-07-30 |
Family
ID=5917126
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1975180819A PL94249B1 (de) | 1974-06-01 | 1975-05-31 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US4017539A (de) |
| JP (1) | JPS516950A (de) |
| AR (1) | AR205644A1 (de) |
| AT (1) | AT343675B (de) |
| BE (1) | BE829499A (de) |
| CA (1) | CA1052391A (de) |
| CS (1) | CS183804B2 (de) |
| DD (1) | DD119225A5 (de) |
| DE (1) | DE2426683A1 (de) |
| FI (1) | FI751528A (de) |
| FR (1) | FR2272652B1 (de) |
| GB (1) | GB1461020A (de) |
| HU (1) | HU168739B (de) |
| NL (1) | NL7506270A (de) |
| PL (1) | PL94249B1 (de) |
| SE (1) | SE7506025L (de) |
| ZA (1) | ZA753355B (de) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS60127996A (ja) * | 1983-12-15 | 1985-07-08 | 松下電器産業株式会社 | 工業用ロボツトの塵埃飛散防止装置 |
| HU196745B (en) * | 1984-04-03 | 1989-01-30 | Chinoin Gyogyszer Es Vegyeszet | Process for producing n-/amino-imino-methyl/-isothiuronium derivatives with immunostimulant and cytostatic effect |
| IL74743A (en) * | 1984-04-03 | 1992-09-06 | Peremartoni Vegyipari Vallalat | Process for the preparation of aminoiminomethyl isothiuronium compounds and salts and pharmaceutical compositions containing them and some novel compounds and salts |
| US6099859A (en) * | 1998-03-20 | 2000-08-08 | Andrx Pharmaceuticals, Inc. | Controlled release oral tablet having a unitary core |
| US6417208B1 (en) * | 1999-02-05 | 2002-07-09 | Albert Einstein College Of Medicine Of Yeshiva University | Method of identification of inhibitors of PDE1C |
| WO2010011860A1 (en) * | 2008-07-23 | 2010-01-28 | Diabetomics, Llc | Methods for detecting pre-diabetes and diabetes |
| CN111848494B (zh) * | 2014-04-17 | 2023-08-01 | 伊谬诺米特医疗有限公司 | 胍化合物及其用途 |
| CN107206351B (zh) * | 2015-02-03 | 2021-03-26 | 圣安德鲁斯大学董事会 | 含no的组合物 |
| RS63558B1 (sr) * | 2016-04-20 | 2022-10-31 | New Frontier Labs Llc | Estri azelainske kiseline u lečenju insulinske rezistencije |
| CN107353232A (zh) * | 2017-06-21 | 2017-11-17 | 成都市考恩斯科技有限责任公司 | 有机物盐形式的硫化氢供体及其制备方法 |
| CN110615886A (zh) * | 2019-09-05 | 2019-12-27 | 哈尔滨工程大学 | 一种双胍衍生物抗菌型环氧树脂固化剂及其制备方法 |
| CN111018748A (zh) * | 2019-12-27 | 2020-04-17 | 广东省生物医药技术研究所 | 化合物(s)-1-(1-萘基)乙基双胍及其制备方法和应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3170925A (en) * | 1965-02-23 | L-subsmtuted | ||
| US3270036A (en) * | 1965-10-07 | 1966-08-30 | Squibb & Sons Inc | Adamantylbiguanides |
| US3471491A (en) * | 1967-08-28 | 1969-10-07 | Squibb & Sons Inc | Adamantyl-s-triazines |
-
1974
- 1974-06-01 DE DE19742426683 patent/DE2426683A1/de active Pending
-
1975
- 1975-01-01 AR AR259024A patent/AR205644A1/es active
- 1975-05-07 US US05/575,098 patent/US4017539A/en not_active Expired - Lifetime
- 1975-05-16 CA CA227,188A patent/CA1052391A/en not_active Expired
- 1975-05-23 GB GB2273175A patent/GB1461020A/en not_active Expired
- 1975-05-26 BE BE156721A patent/BE829499A/xx unknown
- 1975-05-26 FI FI751528A patent/FI751528A/fi not_active Application Discontinuation
- 1975-05-26 ZA ZA00753355A patent/ZA753355B/xx unknown
- 1975-05-27 DD DD186278A patent/DD119225A5/xx unknown
- 1975-05-27 SE SE7506025A patent/SE7506025L/xx not_active Application Discontinuation
- 1975-05-28 NL NL7506270A patent/NL7506270A/xx not_active Application Discontinuation
- 1975-05-30 JP JP50065237A patent/JPS516950A/ja active Pending
- 1975-05-30 CS CS7500003819A patent/CS183804B2/cs unknown
- 1975-05-30 HU HUBO1558A patent/HU168739B/hu unknown
- 1975-05-30 FR FR7516925A patent/FR2272652B1/fr not_active Expired
- 1975-05-30 AT AT412175A patent/AT343675B/de not_active IP Right Cessation
- 1975-05-31 PL PL1975180819A patent/PL94249B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR205644A1 (es) | 1976-05-21 |
| FI751528A (de) | 1975-12-02 |
| CA1052391A (en) | 1979-04-10 |
| NL7506270A (nl) | 1975-12-03 |
| SE7506025L (sv) | 1975-12-02 |
| BE829499A (fr) | 1975-11-26 |
| ZA753355B (en) | 1976-05-26 |
| HU168739B (de) | 1976-07-28 |
| GB1461020A (en) | 1977-01-13 |
| DD119225A5 (de) | 1976-04-12 |
| DE2426683A1 (de) | 1975-12-18 |
| AT343675B (de) | 1978-06-12 |
| FR2272652A1 (de) | 1975-12-26 |
| CS183804B2 (en) | 1978-07-31 |
| US4017539A (en) | 1977-04-12 |
| JPS516950A (de) | 1976-01-20 |
| AU8153675A (en) | 1976-12-02 |
| FR2272652B1 (de) | 1978-10-06 |
| ATA412175A (de) | 1977-10-15 |
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|---|---|---|
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